Solid-phase library synthesis of bi-functional derivatives of oleanolic and maslinic acids and their cytotoxicity on three cancer cell lines

ACS Combinatorial Science

Volumn 16, Issue 8, 2014, Pages 428-447

  Parra, Andres ^a   Martin Fonseca, Samuel ^a   Rivas, Francisco ^a   Reyes Zurita, Fernando J ^a   Medina O'Donnell, Marta ^a   Rufino Palomares, Eva E ^a   Martinez, Antonio ^a   Garcia Granados, Andres ^a   Lupiañez, Jose A ^a   Albericio, Fernando ^b,c  

^a UNIVERSITY OF GRANADA   (Spain)

^b INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^c UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

acylation; combinatorial chemistry; maslinic; oleanolic; solid phase synthesis; triterpene

Indexed keywords

ANTINEOPLASTIC AGENT; MASLINIC ACID; OLEANOLIC ACID; TRITERPENE;

ACYLATION; CHEMISTRY; COMBINATORIAL CHEMISTRY; HUMAN; NEOPLASMS; SOLID PHASE SYNTHESIS; SYNTHESIS; TUMOR CELL LINE;

ACYLATION; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; COMBINATORIAL CHEMISTRY TECHNIQUES; HUMANS; NEOPLASMS; OLEANOLIC ACID; SOLID-PHASE SYNTHESIS TECHNIQUES; TRITERPENES;

EID: 84905868830     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co500051z     Document Type: Article

References (55)

1. Cragg, G. M.; Newman, D. J. Natural Products: A Continuing Source of Novel Drug Leads Biochim. Biophys. Acta 2013, 1830, 3670-3695
2. Dias, D. A.; Urban, S.; Roessner, U. A Historical Overview of Natural Products in Drug Discovery Metabolites 2012, 2, 303-336
3. Ganesan, A. The Impact of Natural Products upon Modern Drug Discovery Curr. Opin. Chem. Biol. 2008, 12, 306-317
4. Newman, D. J.; Cragg, G. M. Natural Products as Sources of New Drugs over the 30 Years from 1981 to 2010 J. Nat. Prod. 2012, 75, 311-335
5. Ngo, L. T.; Okogun, J. I.; Folk, W. R. 21st Century Natural Product Research and Drug Development and Traditional Medicines Nat. Prod. Rep. 2013, 30, 584-592
6. Grabowski, K.; Baringhaus, K.-H.; Schneider, G. Scaffold Diversity of Natural Products: Inspiration for Combinatorial Library Design Nat. Prod. Rep. 2008, 25, 892-904
7. Welsch, M. E.; Snyder, S. A.; Stockwell, B. R. Privileged Scaffolds for Library Design and Drug Discovery Curr. Opin. Chem. Biol. 2010, 14, 347-361
8. Boldi, A. M. Libraries from Natural Product-Like Scaffolds Curr. Opin. Chem. Biol. 2004, 8, 281-286
9. Bannwarth, W.; Hinzen, B. Combinatorial Chemistry: From Theory to Application. In Methods and Principles in Medicinal Chemistry; Mannhold, R.; Kubinyi, H.; Folkers, G., Eds.; Wiley-VCH: Weinheim, Germany, 2006; pp 1-672.
10. Bräse, S. Combinatorial Chemistry on Solid Supports. In Topics in Current Chemistry; Balzani, V.; De Meijere, A.; Houk, K. N.; Kessler, H.; Lehn, J.-M.; Ley, S. V.; Schreiber, S. L.; Thiem, J.; Trost, B. M.; Vögtle, F.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 2007; pp 1-360.
11. Nandy, J. P.; Prakesch, M.; Khadem, S.; Reddy, P. T.; Sharma, U.; Arya, P. Advances in Solution- and Solid-Phase Synthesis toward the Generation of Natural-Product-Like Libraries Chem. Rev. 2009, 109, 1999-2060
12. Mentel, M.; Breinbauer, R. Combinatorial Solid-Phase Natural Product Chemistry Top. Curr. Chem. 2007, 278, 209-241
13. Cironi, P.; Alvarez, M.; Albericio, F. Solid-Phase Chemistry in the Total Synthesis of Non-Peptidic Natural Products Mini-Rev. Med. Chem. 2006, 6, 11-25
14. Ganesan, A. Solid-Phase Synthesis in the Twenty-First Century Mini-Rev. Med. Chem. 2006, 6, 3-10
15. Baxendale, I. R.; Ley, S. V. Synthesis of Alkaloid Natural Products Using Solid-Supported Reagents and Scavengers Curr. Org. Chem. 2005, 9, 1521-1534
16. Eifler-Lima, V. L.; Graebin, C. S.; Uchoa, F. D. T.; Duarte, P. D.; Corrêa, A. G. Highlights in the Solid-Phase Organic Synthesis of Natural Products and Analogues J. Braz. Chem. Soc. 2010, 21, 1401-1423
17. Pathak, A.; Singh, S. K.; Biabani, M. A. F.; Kulshreshtha, D. K.; Puri, S. K.; Srivastava, S.; Kundu, B. Synthesis of Combinatorial Libraries Based on Terpenoid Scaffolds Comb. Chem. High Throughput Screen. 2002, 5, 241-248
18. Hill, R. A.; Connolly, J. D. Triterpenoids Nat. Prod. Rep. 2013, 30, 1028-1065 and references therein.
19. Sultana, N.; Saify, Z. S. Naturally Occurring and Synthetic Agents as Potential Anti-Inflammatory and Immunomodulants Anti-Inflammatory Anti-Allergy Agents Med. Chem. 2012, 11, 3-19
20. Patlolla, J. M. R.; Rao, C. V. Triterpenoids for Cancer Prevention and Treatment: Current Status and Future Prospects Curr. Pharm. Biotechnol. 2012, 13, 147-155
21. Bishayee, A.; Ahmed, S.; Brankov, N.; Perloff, M. Triterpenoids as Potential Agents for the Chemoprevention and Therapy of Breast Cancer Front. Biosci. 2011, 16, 980-996
22. Kuttan, G.; Pratheeshkumar, P.; Manu, K. A.; Kuttan, R. Inhibition of Tumor Progression by Naturally Occurring Terpenoids Pharm. Biol. 2011, 49, 995-1007
23. Cassels, B. K.; Asencio, M. Anti-HIV Activity of Natural Triterpenoids and Hemisynthetic Derivatives 2004-2009 Phytochem. Rev. 2011, 10, 545-564
24. Yadav, V. R.; Prasad, S.; Sung, B.; Kannappan, R.; Aggarwal, B. B. Targeting Inflammatory Pathways by Triterpenoids for Prevention and Treatment of Cancer Toxins 2010, 2, 2428-2466
25. Salvador, J. A. R. Pentacyclic Triterpenes as Promising Agents in Cancer; Cancer Etiology, Diagnosis and Treatments Series; Nova Science Publishers: New York, 2010; pp 1-321.
26. Wolska, K. I.; Grudniak, A. M.; Fiecek, B.; Kraczkiewicz-Dowjat, A.; Kurek, A. Antibacterial Activity of Oleanolic and Ursolic Acids and Their Derivatives Cent. Eur. J. Biol. 2010, 5, 543-553
27. Rios, J. Effects of Triterpenes on the Immune System J. Ethnopharmacol. 2010, 128, 1-14
28. Feng, J.; Chen, W.; Zhao, Y.; Ju, X. Anti-Tumor Activity of Oleanolic, Ursolic and Glycyrrhetinic Acid Open Nat. Prod. J. 2009, 2, 48-52
29. Laszczyk, M. N. Pentacyclic Triterpenes of the Lupane, Oleanane, and Ursane Group as Tools in Cancer Therapy Planta Med. 2009, 75, 1549-1560
30. Dzubak, P.; Hajduch, M.; Vydra, D.; Hustova, A.; Kvasnica, M.; Biedermann, D.; Markova, L.; Urban, M.; Sarek, J. Pharmacological Activities of Natural Triterpenoids and Their Therapeutic Implications Nat. Prod. Rep. 2006, 23, 394-411 and references therein.
31. Sporn, M. B.; Liby, K. T. Synthetic Oleanane Triterpenoids: Multifunctional Drugs with a Broad Range of Applications for Prevention and Treatment of Chronic Disease Pharmacol. Rev. 2012, 64, 972-1003
32. Sporn, M. B.; Liby, K. T.; Yore, M. M.; Fu, L.; Lopchuck, J. M.; Gribble, G. New Synthetic Triterpenoids: Potent Agents for Prevention and Treatment of Tissue Injury Caused by Inflammatory and Oxidative Stress J. Nat. Prod. 2011, 74, 537-545
33. Kuo, R.-Y.; Qian, K.; Morris-Natschke, S. L.; Lee, K.-H. Plant-Derived Triterpenoids and Analogues as Antitumor and Anti-HIV Agents Nat. Prod. Rep. 2009, 26, 1321-1344
34. Silva, G. N. S.; Maria, N. R. G.; Schuck, D. C.; Cruz, L. N.; Moraes, M. S.; Nakabashi, M.; Graebin, C.; Gosmann, G.; Garcia, C. R. S.; Gnoatto, S. C. B. Two Series of New Semisynthetic Triterpene Derivatives: Differences in Anti-Malarial Activity, Cytotoxicity and Mechanism of Action Malaria J. 2013, 12, 89-95
35. Kumar, A.; Shah, B. A.; Singh, S.; Hamid, A.; Singh, S. K.; Sethi, V. K.; Saxena, A. K.; Singh, J.; Taneja, S. C. Acyl Derivatives of Boswellic Acids as Inhibitors of NF-B and STATs Bioorg. Med. Chem. Lett. 2012, 22, 431-435
36. Ahmad, F. B. H.; Moghaddam, M. G.; Basri, M.; Rahman, M. B. A. Anticancer Activity of 3- O -Acylated Betulinic Acid Derivatives Obtained by Enzymatic Synthesis Biosci. Biothechnol. Biochem. 2010, 74, 1025-1029
37. Drag-Zalesinska, M.; Kulbacka, J.; Saczko, J.; Wysocka, T.; Zabel, M.; Surowiak, P.; Drag, M. Esters of Betulin and Betulinic Acid with Amino Acids have improved Water Solubility and are Selectively Cytotoxic toward Cancer Cells Bioorg. Med. Chem. Lett. 2009, 19, 4814-4817
38. Soldi, C.; Pizzolatti, M. G.; Luiz, A. P.; Marcon, R.; Meotti, F. V.; Mioto, L. A.; Santos, A. R. S. Synthetic Derivatives of the - and β-Amyrin Triterpenes and Their Antinociceptive Properties Bioorg. Med. Chem. 2008, 16, 3377-3386
39. Qian, K.; Nakagawa-Goto, K.; Yu, D.; Morris-Natschke, S. L.; Nitz, T. J.; Kilgore, N.; Allaway, G. P.; Lee, K. H. Anti-AIDS agents 73: Structure-Activity Relationship Study and Asymmetric Synthesis of 3- O -Monomethylsuccinyl- Betulinic Acid Derivatives Bioorg. Med. Chem. Lett. 2007, 17, 6553-6557
40. Huang, L.; Ho, P.; Lee, K.-H.; Chen, C.-H. Synthesis and Anti-HIV Activity of Bi-Functional Betulinic Acid Derivatives Bioorg. Med. Chem. 2006, 14, 2279-2289
41. Tolstikovaa, T. G.; Sorokinaa, I. V.; Tolstikova, G. A.; Tolstikovb, A. G.; Flekhter, O. B. Biological Activity and Pharmacological Prospects of Lupane Terpenoids: II. Semisynthetic Lupane Derivatives Russ. J. Bioorg. Chem. 2006, 32, 261-276
42. Zhang, Y.; Li, J.-X.; Zhao, J.; Wang, S.-Z.; Pan, Y.; Tanaka, K.; Kadota, S. Synthesis and Activity of Oleanolic Acid Derivatives, A Novel Class of Inhibitors of Osteoclast Formation Bioorg. Med. Chem. Lett. 2005, 15, 1629-1632
43. Kashiwada, Y.; Sekiya, M.; Ikeshiro, Y.; Fujioka, T.; Kilgore, N. R.; Wild, C. T.; Allaway, G. P.; Lee, K.-H. 3- O -Glutaryl-Dihydrobetulin and Related Monoacyl Derivatives as Potent Anti-HIV Agents Bioorg. Med. Chem. Lett. 2004, 14, 5851-5853
44. Parra, A.; Rivas, F.; Lopez, P. E.; Garcia-Granados, A.; Martinez, A.; Albericio, F.; Marquez, N.; Muñoz, E. Solution- and Solid-Phase Synthesis and Anti-HIV Activity of Maslinic Acid Derivatives Containing Amino Acids and Peptides Bioorg. Med. Chem. 2009, 17, 1139-1145
45. Parra, A.; Rivas, F.; Martin-Fonseca, S.; Garcia-Granados, A.; Martinez, A. Maslinic Acid Derivatives Induce Significant Apoptosis in B16f10 Murine Melanoma Cells Eur. J. Med. Chem. 2011, 46, 5991-6001
46. Parra, A.; Martin-Fonseca, S.; Rivas, F.; Reyes-Zurita, F. J.; Medina-ODonnell, M.; Martinez, A.; Garcia-Granados, A.; Lupiañez, J. A.; Albericio, F. Semi-Synthesis of Acylated Triterpenes from Olive-Oil Industry Wastes for the Development of Anticancer and Anti-HIV Agents Eur. J. Med. Chem. 2014, 74, 278-301
47. Pollier, J.; Goossens, A. Oleanolic Acid Phytochemistry 2012, 77, 10-15
48. Garcia-Granados, A.; Martinez, A.; Moliz, J. N.; Parra, A.; Rivas, F. 3β-Hydroxyolean-12-en-28-oic Acid (Oleanolic Acid) Molecules 1998, 3, M87
49. Garcia-Granados, A.; Martinez, A.; Moliz, J. N.; Parra, A.; Rivas, F. 2,3β-Dihydroxyolean-12-en-28-oic Acid (Maslinic Acid) Molecules 1998, 3, M88
50. Sanchez-Quesada, C.; Lopez-Biedma, A.; Warleta, F.; Campos, M.; Beltran, G.; Gaforio, J. J. Bioactive Properties of the Main Triterpenes Found in Olives, Virgin Olive Oil, and Leaves of Olea europaea J. Agric. Food Chem. 2013, 61, 12173-12182 and references therein.
51. Preedy, V. R.; Watson, R. R., Eds. Olives and Olive Oil in Health and Disease Prevention; Elsevier: London, 2010; pp 1-1479.
52. Sultana, N.; Ata, A. Oleanolic Acid and Related Derivatives as Medicinally Important Compounds J. Enzyme Inhib. Med. Chem. 2008, 23, 739-756
53. Garcia-Granados, A. Process for the Industrial Recovery of Oleanolic and Maslinic Acids Contained in the Olive Milling Byproducts. PCT. Int. Appl. WO 9804331, 1998.
54. Reyes, F. J.; Centelles, J. J.; Lupiañez, J. A.; Cascante, M. (2,3β)-2,3-Dihydroxyolean-12-en-28-oic Acid, a New Natural Triterpene from Olea europaea, Induces Caspase Dependent Apoptosis Selectively in Colon Adenocarcinoma Cells FEBS Lett. 2006, 580, 6302-6310
55. Martinez, A.; Rivas, F.; Perojil, A.; Parra, A.; Garcia-Granados, A.; Fernandez-Vivas, A. Biotransformation of Oleanolic and Maslinic Acids by Rhizomucor miehei Phytochemistry 2013, 94, 229-237